(2-Methyl-1-phenylsulfonyl-1H-indol-3-yl)methanol

In the title compound, C16H15NO3S, the plane of the phenyl ring forms a dihedral angle of 80.37 (8)° with the indole ring system. The crystal packing is stabilized by weak O—H⋯O hydrogen bonds which link the molecules into infinite chains along the a axis of the crystal.

In the title compound, C 16 H 15 NO 3 S, the plane of the phenyl ring forms a dihedral angle of 80.37 (8) with the indole ring system. The crystal packing is stabilized by weak O-HÁ Á ÁO hydrogen bonds which link the molecules into infinite chains along the a axis of the crystal. Mo K radiation = 0.23 mm À1 T = 295 (2) Table 1 Hydrogen-bond geometry (Å , ).

Comment
In continuation of our studies of benzenesulfonamide derivatives, which are known to exhibit antibacterial (Nieto et al., 2005), anticancer and anti -HIV (Pomarnacka & Kozlarska-Kedra, 2003) activities, we determined the crystal structure of the title compound, (I). The geometric parameters of the molecule of (I) (Fig. 1) agree well with those reported for similar structures (Chakkaravarthi et al., 2007;Liu et al., 2007).
The plane of the phenyl ring forms the dihedral angle of 80.37 (8)° with the indole ring system. The N1-S1-C1 plane is also approximately orthogonal to indole (dihedral angle 79.21 (6)°) and makes an angle of 57.86 (11)° with the phenyl plane.
The crystal packing of (I) is stabilized by a rather weak O-H···O bonds which link the molecules into the infinite chains along the x-axis of the crystal (Fig. 2, Table 2).

Experimental
Benzenesulfonyl chloride (7.75 ml, 43.9 mmol), 60% NaOH solution (60 g in 100 ml), along with tetrabutylammonium hydrogensulfate (1.5 g) were added to the solution of 2-methylindole-3-carboxaldehyde (8.0 g, 50.3 mmol) in distilled benzene (200 ml). The two-phase system thus formed was stirred at room temperature for 2 h. It was then diluted with water (200 ml) and the organic layer was separated. The aqueous layer was extracted with benzene (two times by 30 ml).
The combined organic layer was dried (Na 2 SO 4 ). The benzene was then completely removed and the crude product was recrystallized from methanol to get 1-phenylsulfonyl-2-methylindole-3-carboxaldehyde.
NaBH 4 (2.97 g, 78.60 mmol) was added slowly to a solution of 1-phenylsulfonyl-2-methylindole-3-carboxaldehyde (3 g, 13.10 mmol) in THF (30 ml). The reaction mixture was stirred at room temperature for 3 hrs. Dilute HCl (10%) was cautiously added until the solution became acidic. After most of the THF was removed in vacuo, the solution was extracted with dichloromethane and dried (MgSO 4 ); the solvent was then removed under vacuo. The crude product thus obtained was recrystallized from 10% ethyl acetate/n-hexane.

Refinement
H atoms were positioned geometrically and refined using riding model approximation with C-H = 0.93 Å and U iso (H) = 1.2Ueq(C) for aromatic C-H, C-H = 0.97 Å and U iso (H) = 1.2Ueq(C) for CH 2 , C-H = 0.96 Å and U iso (H) = 1.5Ueq(C) for CH 3 and O-H = 0.82 Å and U iso (H) = 1.5Ueq(O) for OH. The hydroxyl O3 atom showed rather high thermal displacement parameters, however the attempts to introduce an alternative position and refine disordered model proved unsuccessful. Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids; H atoms are shown as small spheres of arbitrary radius. (2-Methyl-1-phenylsulfonyl-1H-indol-3-yl)methanol